#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:53:12 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179082 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/44/4304454.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4304454
loop_
_publ_author_name
'Joe B. Gilroy'
'Peter O. Otieno'
'Michael J. Ferguson'
'Robert McDonald'
'Robin G. Hicks'
_publ_section_title
;
Synthesis and Characterization of 3-Cyano- and 3-Nitroformazans,
Nitrogen-Rich Analogues of β-Diketimine Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1279
_journal_page_last               1286
_journal_paper_doi               10.1021/ic7019445
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C19 H23 N5 O2'
_chemical_formula_sum            'C19 H23 N5 O2'
_chemical_formula_weight         353.42
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.929(2)
_cell_angle_beta                 78.539(2)
_cell_angle_gamma                63.853(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9215(13)
_cell_length_b                   9.2825(14)
_cell_length_c                   12.9559(19)
_cell_measurement_reflns_used    2584
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.47
_cell_volume                     934.9(2)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7271
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9486
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker SHELXTL (Bruker, 1997)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0737P)²+0.2493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                2722
_reflns_number_total             3766
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic7019445-file005.cif
_cod_data_source_block           vic0712
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4304454
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.92788(18) -0.32622(19) 0.20065(12) 0.0565(4) Uani 1 1 d . . .
O2 O 0.80414(19) -0.42609(18) 0.33755(13) 0.0602(4) Uani 1 1 d . . .
N1 N 0.65832(19) -0.06044(19) 0.17851(12) 0.0389(4) Uani 1 1 d . . .
N2 N 0.5288(2) 0.07819(19) 0.16810(12) 0.0414(4) Uani 1 1 d . . .
H2N H 0.4458 0.1056 0.2201 0.050 Uiso 1 1 calc R . .
N3 N 0.55063(18) -0.15047(18) 0.35905(12) 0.0357(4) Uani 1 1 d . . .
N4 N 0.41857(19) -0.01653(18) 0.36076(11) 0.0359(4) Uani 1 1 d . . .
N5 N 0.8079(2) -0.3145(2) 0.26880(13) 0.0434(4) Uani 1 1 d . . .
C1 C 0.6587(2) -0.1593(2) 0.26826(14) 0.0362(4) Uani 1 1 d . . .
C11 C 0.5238(2) 0.1851(2) 0.07101(13) 0.0362(4) Uani 1 1 d . . .
C12 C 0.6637(2) 0.2178(2) 0.02530(14) 0.0387(4) Uani 1 1 d . . .
C13 C 0.6489(3) 0.3227(2) -0.06957(14) 0.0427(5) Uani 1 1 d . . .
H13 H 0.7425 0.3460 -0.1022 0.051 Uiso 1 1 calc R . .
C14 C 0.5045(3) 0.3945(2) -0.11844(14) 0.0429(5) Uani 1 1 d . . .
C15 C 0.3668(3) 0.3635(3) -0.06890(15) 0.0450(5) Uani 1 1 d . . .
H15 H 0.2651 0.4153 -0.1004 0.054 Uiso 1 1 calc R . .
C16 C 0.3739(3) 0.2584(2) 0.02578(15) 0.0422(5) Uani 1 1 d . . .
C17 C 0.8214(3) 0.1506(3) 0.07738(18) 0.0558(6) Uani 1 1 d . . .
H17A H 0.7920 0.1637 0.1529 0.067 Uiso 1 1 calc R . .
H17B H 0.8909 0.2088 0.0429 0.067 Uiso 1 1 calc R . .
H17C H 0.8844 0.0352 0.0704 0.067 Uiso 1 1 calc R . .
C18 C 0.4949(3) 0.5064(3) -0.22205(16) 0.0590(6) Uani 1 1 d . . .
H18A H 0.4254 0.4929 -0.2658 0.071 Uiso 1 1 calc R . .
H18B H 0.6084 0.4802 -0.2600 0.071 Uiso 1 1 calc R . .
H18C H 0.4448 0.6188 -0.2077 0.071 Uiso 1 1 calc R . .
C19 C 0.2229(3) 0.2243(3) 0.07490(18) 0.0636(7) Uani 1 1 d . . .
H19A H 0.1702 0.2790 0.1381 0.076 Uiso 1 1 calc R . .
H19B H 0.2585 0.1072 0.0952 0.076 Uiso 1 1 calc R . .
H19C H 0.1418 0.2645 0.0233 0.076 Uiso 1 1 calc R . .
C21 C 0.2997(2) 0.0010(2) 0.45298(13) 0.0312(4) Uani 1 1 d . . .
C22 C 0.2757(2) -0.1291(2) 0.52147(13) 0.0329(4) Uani 1 1 d . . .
C23 C 0.1477(2) -0.0913(2) 0.60578(13) 0.0357(4) Uani 1 1 d . . .
H23 H 0.1298 -0.1775 0.6525 0.043 Uiso 1 1 calc R . .
C24 C 0.0451(2) 0.0662(2) 0.62472(13) 0.0364(4) Uani 1 1 d . . .
C25 C 0.0718(2) 0.1908(2) 0.55553(14) 0.0375(4) Uani 1 1 d . . .
H25 H 0.0025 0.2995 0.5676 0.045 Uiso 1 1 calc R . .
C26 C 0.1959(2) 0.1620(2) 0.46967(14) 0.0349(4) Uani 1 1 d . . .
C27 C 0.3723(3) -0.3037(2) 0.50491(15) 0.0427(5) Uani 1 1 d . . .
H27A H 0.3813 -0.3129 0.4297 0.051 Uiso 1 1 calc R . .
H27B H 0.3134 -0.3675 0.5484 0.051 Uiso 1 1 calc R . .
H27C H 0.4852 -0.3447 0.5258 0.051 Uiso 1 1 calc R . .
C28 C -0.0929(3) 0.1011(3) 0.71669(15) 0.0484(5) Uani 1 1 d . . .
H28A H -0.1168 0.0054 0.7424 0.058 Uiso 1 1 calc R . .
H28B H -0.1946 0.1929 0.6933 0.058 Uiso 1 1 calc R . .
H28C H -0.0571 0.1278 0.7742 0.058 Uiso 1 1 calc R . .
C29 C 0.2200(3) 0.3021(2) 0.39718(17) 0.0509(5) Uani 1 1 d . . .
H29A H 0.1748 0.3195 0.3304 0.061 Uiso 1 1 calc R . .
H29B H 0.3402 0.2777 0.3823 0.061 Uiso 1 1 calc R . .
H29C H 0.1605 0.4002 0.4317 0.061 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 117.81(15) . . ?
N1 N2 C11 118.79(15) . . ?
N4 N3 C1 114.44(15) . . ?
N3 N4 C21 117.55(14) . . ?
O1 N5 O2 123.61(17) . . ?
O1 N5 C1 118.77(17) . . ?
O2 N5 C1 117.62(15) . . ?
N1 C1 N3 134.26(17) . . ?
N1 C1 N5 112.75(15) . . ?
N3 C1 N5 112.97(16) . . ?
C16 C11 C12 121.82(17) . . ?
C16 C11 N2 117.45(16) . . ?
C12 C11 N2 120.70(17) . . ?
C13 C12 C11 117.19(18) . . ?
C13 C12 C17 120.15(17) . . ?
C11 C12 C17 122.61(17) . . ?
C14 C13 C12 122.83(18) . . ?
C13 C14 C15 118.29(18) . . ?
C13 C14 C18 120.93(19) . . ?
C15 C14 C18 120.8(2) . . ?
C14 C15 C16 121.69(19) . . ?
C15 C16 C11 118.12(18) . . ?
C15 C16 C19 119.84(19) . . ?
C11 C16 C19 122.02(18) . . ?
C26 C21 C22 120.69(16) . . ?
C26 C21 N4 114.78(15) . . ?
C22 C21 N4 124.41(15) . . ?
C23 C22 C21 117.50(16) . . ?
C23 C22 C27 118.22(16) . . ?
C21 C22 C27 124.16(16) . . ?
C24 C23 C22 122.92(16) . . ?
C23 C24 C25 117.94(16) . . ?
C23 C24 C28 120.99(17) . . ?
C25 C24 C28 121.06(18) . . ?
C26 C25 C24 122.19(17) . . ?
C25 C26 C21 118.74(16) . . ?
C25 C26 C29 119.97(17) . . ?
C21 C26 C29 121.28(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N5 1.225(2) . ?
O2 N5 1.225(2) . ?
N1 N2 1.299(2) . ?
N1 C1 1.322(2) . ?
N2 C11 1.425(2) . ?
N3 N4 1.282(2) . ?
N3 C1 1.357(2) . ?
N4 C21 1.416(2) . ?
N5 C1 1.468(2) . ?
C11 C16 1.392(3) . ?
C11 C12 1.402(3) . ?
C12 C13 1.388(3) . ?
C12 C17 1.501(3) . ?
C13 C14 1.377(3) . ?
C14 C15 1.388(3) . ?
C14 C18 1.508(3) . ?
C15 C16 1.391(3) . ?
C16 C19 1.507(3) . ?
C21 C26 1.405(2) . ?
C21 C22 1.412(2) . ?
C22 C23 1.390(2) . ?
C22 C27 1.503(2) . ?
C23 C24 1.385(3) . ?
C24 C25 1.386(3) . ?
C24 C28 1.506(2) . ?
C25 C26 1.382(2) . ?
C26 C29 1.508(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N N4 0.88 1.97 2.615(2) 129.4 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C11 -178.48(16) . . . . ?
C1 N3 N4 C21 179.76(15) . . . . ?
N2 N1 C1 N3 -0.9(3) . . . . ?
N2 N1 C1 N5 177.55(15) . . . . ?
N4 N3 C1 N1 -1.2(3) . . . . ?
N4 N3 C1 N5 -179.65(15) . . . . ?
O1 N5 C1 N1 14.3(2) . . . . ?
O2 N5 C1 N1 -165.06(17) . . . . ?
O1 N5 C1 N3 -166.85(16) . . . . ?
O2 N5 C1 N3 13.8(2) . . . . ?
N1 N2 C11 C16 134.58(19) . . . . ?
N1 N2 C11 C12 -47.3(2) . . . . ?
C16 C11 C12 C13 -2.2(3) . . . . ?
N2 C11 C12 C13 179.75(15) . . . . ?
C16 C11 C12 C17 174.91(19) . . . . ?
N2 C11 C12 C17 -3.1(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C17 C12 C13 C14 -176.76(18) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C12 C13 C14 C18 -179.38(18) . . . . ?
C13 C14 C15 C16 -2.3(3) . . . . ?
C18 C14 C15 C16 178.86(18) . . . . ?
C14 C15 C16 C11 0.6(3) . . . . ?
C14 C15 C16 C19 -178.1(2) . . . . ?
C12 C11 C16 C15 1.7(3) . . . . ?
N2 C11 C16 C15 179.82(16) . . . . ?
C12 C11 C16 C19 -179.7(2) . . . . ?
N2 C11 C16 C19 -1.6(3) . . . . ?
N3 N4 C21 C26 156.47(16) . . . . ?
N3 N4 C21 C22 -27.3(3) . . . . ?
C26 C21 C22 C23 -0.7(3) . . . . ?
N4 C21 C22 C23 -176.66(16) . . . . ?
C26 C21 C22 C27 175.35(17) . . . . ?
N4 C21 C22 C27 -0.6(3) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C27 C22 C23 C24 -176.39(17) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C22 C23 C24 C28 179.53(16) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C28 C24 C25 C26 -179.02(17) . . . . ?
C24 C25 C26 C21 -0.9(3) . . . . ?
C24 C25 C26 C29 -179.77(18) . . . . ?
C22 C21 C26 C25 1.2(3) . . . . ?
N4 C21 C26 C25 177.51(16) . . . . ?
C22 C21 C26 C29 -179.95(18) . . . . ?
N4 C21 C26 C29 -3.6(3) . . . . ?
